Crystalline form v of melanocortin receptor agonist compound, and method for preparing same

Abstract

The present invention relates to a crystalline form V of a compound represented by chemical formula 1, a method for preparing same, and a pharmaceutical composition comprising same. Crystalline form V of the compound represented by chemical formula 1 according to the present invention may be characterized by an XRD pattern, a DSC profile, and/or a TGA profile.

1 . A crystalline form V of a compound of the following formula 1, a pharmaceutically acceptable salt thereof, or a solvate thereof, wherein the crystalline form V has an X-ray powder diffraction pattern comprising 3 or more characteristic peaks selected from peaks with the following diffraction angles (2θ values) of: 4.42±0.2°, 4.92±0.2°, 7.20±0.2°, 7.84±0.2°, 9.22±0.2°, 12.22±0.2°, 12.58±0.2°, 16.20±0.2°, 16.48±0.2°, 17.72±0.2°, 20.24±0.2°, 20.08±0.2°, and 23.65±0.2°, 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is a C 2 -C 5  alkyl. 
       
     
     
         2 . The crystalline form V of  claim 1 , wherein the X-ray powder diffraction pattern has characteristic peaks including the following diffraction angles (2θ values): 4.42±0.2°, 7.84±0.2°, 12.58±0.2°, 16.20±0.2°, 20.08±0.2°, and 23.65±0.2°. 
     
     
         3 . The crystalline form V of  claim 1 , wherein the X-ray powder diffraction pattern has characteristic peaks including the following diffraction angles (2θ values): 4.92±0.2°, 7.20±0.2°, 9.22±0.2°, 12.22±0.2°, 16.48±0.2°, 17.72±0.2°, and 20.24±0.2°. 
     
     
         4 . The crystalline form V of  claim 1 , wherein the pharmaceutically acceptable salt of the compound of the formula 1 is selected from the group consisting of: hydrochloride, sulfate, nitrate, phosphate, hydrobromide, and hydroiodide, of the compound of the formula 1. 
     
     
         5 . The crystalline form V of  claim 1 , which is a crystalline form of a solvate of hydrochloride of the compound of the formula 1. 
     
     
         6 . The crystalline form V of  claim 5 , wherein the solvate is a solvate with an aromatic ether. 
     
     
         7 . The crystalline form V of  claim 6 , wherein the solvate is a solvate with methyl phenyl ether. 
     
     
         8 . A method for preparing the crystalline form V of  claim 1 , the method comprising the steps of:
 preparing a mixed solution by dissolving the compound of the formula 1 in a crystallization solvent containing an aromatic ether; and   obtaining crystals from the mixed solution.   
     
     
         9 . The method for preparing the crystalline form V of  claim 8 , wherein the crystallization solvent further includes an aliphatic aprotic organic solvent. 
     
     
         10 . The method for preparing the crystalline form V of  claim 8 , wherein the aromatic ether includes methyl phenyl ether, ethyl phenyl ether, diphenyl ether, or a mixture thereof. 
     
     
         11 . The method for preparing the crystalline form V of  claim 9 , wherein the aliphatic aprotic organic solvent includes diethyl ether, pentane, hexane, heptane, cyclohexane, or a mixture thereof. 
     
     
         12 . The method for preparing the crystalline form V of  claim 9 , wherein the crystallization solvent comprises the aromatic ether and the aliphatic aprotic organic solvent in a volume ratio of 1:1 to 1:10. 
     
     
         13 . The method for preparing the crystalline form V of  claim 8 , further comprising a step for washing the obtained crystals with an aliphatic ether solvent. 
     
     
         14 . The method for preparing the crystalline form V of  claim 13 , wherein the crystallization solvent further includes an aliphatic aprotic organic solvent, and
 the aliphatic aprotic organic solvent included in the crystallization solvent is the same as or different from the aliphatic ether solvent used in the washing step.   
     
     
         15 . The method for preparing the crystalline form V of  claim 14 , wherein the crystallization solvent includes methyl phenyl ether and diethyl ether, and
 the washing solvent includes diethyl ether.   
     
     
         16 . The method for preparing the crystalline form V of  claim 13 , wherein the washing step includes washing the obtained crystals with an aliphatic aprotic organic solvent at least once, and then obtaining crystals at 0° C. to 200° C. 
     
     
         17 . A pharmaceutical composition comprising the crystalline form V of  claim 1 , and a pharmaceutically acceptable carrier. 
     
     
         18 . A pharmaceutical composition comprising the crystalline form V of  claim 1 , and a pharmaceutically acceptable carrier. 
     
     
         19 . (canceled) 
     
     
         20 . A method for agonizing the function of a melanocortin-4 receptor, comprising administering to a subject in need thereof an effective amount of the crystalline form V of  claim 1 . 
     
     
         21 . A method for preventing or treating obesity, diabetes, inflammation, or erectile dysfunction, comprising administering to a subject in need thereof a therapeutically effective amount of the crystalline form V of  claim 1 .